2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 13036549, compound

HRID 1980039Notes

Reaction equation

HRID 1980039 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])[CH3:3].Cl.[CH3:14][O:15][C:16](=[O:26])[C@H:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:18].C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>C(Cl)Cl>[CH3:14][O:15][C:16](=[O:26])[C@H:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:18][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 13036549HCID 13036549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Boc-glycine (1.75 g, 1.00×10-2 mole), L-phenylalanine methyl ester hydrochloride (2.16 g, 1.00×10-2 mole), and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (2.47 g, 1.00×10-2 mole), and CH2Cl2 (50 ml) are stirred at room temperature for 16 hours. The reaction mixture is then washed in turn with 0.5M aqueous HCl (2 times) and saturated aqueous NaHCO3 before being dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate gives 6a as an extremely viscous, almost colorless oil, which was shown to be homogeneous by TLC on silica gel plates and the structure corroborated by NMR. NMR (CDCl3) δ 1.42 (S, 9, t-boc), 3.02 (d,2, benzylic methylene), 3.59 (S, 3, ester), 7.13 (S, 5, aromatic).

Workup

  1. washThe reaction mixture is then washed in turn with 0.5M aqueous HCl (2 times) and saturated aqueous NaHCO3
  2. dry with materialbefore being dried over Na2SO4
  3. filtrationFiltration of the drying agent and evaporation of the filtrate

Sources & evidence

ORD record
ord-fc180684cd3b46069c5434d5df6be99e
Source dataset
uspto-grants-1984_11
Patent number
US04483988

Reaction notes

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